Guesthouse vacation rentals in Downtown San Jose

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Top-rated guesthouse rentals in Downtown San Jose

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Guest favorite

A outdoor shopping area is featured, showcasing a central fountain surrounded by lush landscaping. Several businesses are visible, including a casual dining restaurant and a café. The buildings exhibit a Mediterranean architectural style, complemented by palm trees and clear blue skies.

Guesthouse in Santa Clara

4.92 out of 5 average rating, 144 reviews

Entire guesthouse Santa Clara smart lock entrance.

New remodeled clean and cozy guesthouse in a prime location of Silicon Valley. You will be close to everything when you stay here. Minutes drive to the best Bay Area shopping and dining experiences Santana row and Westfield Valley Fair. Nividia 7min. drive, Apple Park 11 min. drive, Google headquarters Mountain View 15min. Sap center, Levi’s Stadium, and Great America are all nearby. Walk to shops, restaurants and Target shopping center. A close 10 minute drive to San Jose International Airport.

Guest favorite

A hot tub is seen surrounded by a softly lit patio, with colorful string lights enhancing the evening ambiance. Lush greenery and a covered seating area are visible in the background, contributing to a relaxing outdoor space.

Guesthouse in Los Gatos

4.92 out of 5 average rating, 359 reviews

Los Gatos/Cambrian COTTAGE-HOT TUB/pvt.parking

This charming cottage, located on the outskirts of Los Gatos in the quiet and safe Cambrian neighborhood, is an ideal retreat away from the busy downtown. We ensure a safe and comfortable stay with rigorous cleaning protocols. The studio features one queen bed, with an additional cot available upon request. Please note that dogs are on the property. All dogs, including service dogs, must have prior consent from the host and provide current vaccinations (rabies, DH2PP, bordetella, leptospiros.

Guest favorite

Guesthouse in Palo Alto

4.77 out of 5 average rating, 164 reviews

Sunnystay: Bright Garden Palo Alto Studio Cottage

Brand New Remodeled Updated Charming extremely well lit Independent Private Guest cottage with New Bed , Bedding, New Hardwood floors, Remodeled Private bath, Added new Full Kitchen, & Washer Dryer facility in a serene garden setting desirable Crescent Park Palo Alto. Guests have the entire cottage to themselves with a private patio. We have fully upgraded the cottage and addressed all issues from past listing of 3 years ago. Extremely serene and quiet environment, a dream for remote work.

Top guest favorite

The guest house is illuminated at night, revealing a stone patio with a fire pit surrounded by metal chairs. Lush greenery and low lights enhance the outdoor space, while the modern guest house features large glass doors that provide a connection to the garden.

Guesthouse in Rose Garden

4.96 out of 5 average rating, 112 reviews

Garden Cottage w/ Hot Tub • 3 mi. to SJC

This new construction guest house is behind my home, a historic landmark Tudor in San Jose's Rose Garden neighborhood. The space is sun-filled and indoor-outdoor with beautiful garden views. The neighborhood is quiet, the street is shaded by an allée of 85-year old sycamore trees. Your stay comes with hot tub use, a full kitchen, and freshly ground Peet's coffee. 1.5 miles to SAP 1.5 miles to Santana Row & Valley Fair Mall 2 miles to SCU 0.5 miles to Municipal Rose Garden 12 minutes to Levi’s

Top guest favorite

Tall redwood trees create a serene forest environment, with their textured trunks standing closely together. Lush green foliage is visible at the base, complementing the rich earth tones of the bark. A stone wall subtly outlines the natural space, adding to the peaceful atmosphere.

Guesthouse in Boulder Creek

4.99 out of 5 average rating, 218 reviews

Digital Nomad Retreat

Imagine yourself in the REDWOOD FOREST and take a breath of mountain air. Only 25 miles from the Silicon Valley, 15 miles from the Santa Cruz Boardwalk, a cozy location tucked in the forest. Many are on the move and can work from anywhere, so why not a beautiful place of your own? A perfect getaway spot central to WINE TASTING, HIKING, BEACHES and even mountain exploration, right from the doorstep. Located only a mile and a half from downtown Boulder Creek, food and window shopping are easy.

Top guest favorite

Guesthouse in Menlo Park

4.94 out of 5 average rating, 154 reviews

Luxury Guesthouse in the heart of Silicon Valley

BEST Airbnb: Style, Comfort, Location. 1 bedroom, gorgeous bathroom, full kitchen, coffee machine, well-stocked pantry, dining set, comfy sofa & ottoman. Luxury shower: rain, cascade or handheld. Mirror with backlight. Smart TV 50". Broadband. Basic cable. Nest heater/ fan. Hardwood floors. Portable Dyson aircon. Private entry. Automatic entry lights on walkway, wisteria trellis. Dedicated parking. Organic vegetable and fruit garden. Patio. NOTE: a 12.5% tax will be added as a fee.

Guest favorite

A welcoming entrance to the guest house is shown, featuring a solid black door with glass panels. A stylish doormat greets guests, while surrounding greenery adds a touch of nature. A pathway made of brick leads to the door, enhancing the inviting ambiance.

Guesthouse in Palo Alto

4.91 out of 5 average rating, 188 reviews

Downtown Palo Alto Gem! Cute, Spotless Guest House

We invite you to stay in our private, remodeled guest house. It's an easy walk to the restaurants and shops on University Avenue, in a safe and sought-after neighborhood in Downtown Palo Alto. The guest house was recently renovated and has a gorgeous bay window, air conditioning, two skylights, and a spa-like bathroom. We pride ourselves in keeping it absolutely spotless. The studio cottage is 200 square feet. It’s perfect for a single person but can also accommodate a couple.

Top guest favorite

A serene outdoor space features a small table with two wicker chairs surrounded by lush greenery and various shrubs. A pathway winds through the garden, leading to the rustic cottage and sunlit windows. Natural elements enhance the tranquil atmosphere.

Guesthouse in Palo Alto

4.98 out of 5 average rating, 257 reviews

*Airbnb PLUS* Mod Bungalow in Urban Farm Setting

Enjoy a private, high-quality designer experience on a rustic "urban farm". Make yourself at home amidst Mid-Century Modern furniture, a fully-stocked kitchen and luxurious bedding. Grill or hang out on a private patio. Families, friends, or business travelers will appreciate the proximity to downtown Palo Alto, Stanford, and tech companies. Safe and friendly neighborhood. We share fresh eggs from our chickens when in season. Private entrance and off-street parking for one car.

Guest favorite

A serene outdoor space is depicted, featuring a rectangular pool surrounded by a stone deck. White lounge chairs are placed poolside under the shade of trees. A gazebo with seating is visible, and decorative pots with greenery add to the natural atmosphere.

Guesthouse in Monte Sereno

4.9 out of 5 average rating, 208 reviews

Greenwood Guest House, a Peaceful Oasis

Welcome to Greenwood Guest House, a 1 bedroom, 1 bath private house situated in a peaceful and expansive backyard with a pool, tennis court, and beautiful scenery. Our space is a good fit for business trips, couple vacations, and family visits. The kitchenette and laundry room make longer stays quite enjoyable. Easy access to Highway 17 and 85, 15 minute drive to San Jose airport (SJC) and 2 minute drives to either downtown Los Gatos or Saratoga.

Superhost

A wooden double gate made of weathered boards stands closed, leading to the property. The gate is flanked by low greenery, and a concrete pathway is visible beneath it. The surrounding area features a mix of residential structures and trees, indicating a well-maintained environment.

Guesthouse in Downtown San Jose

4.78 out of 5 average rating, 483 reviews

Beautiful private guest house in downtown San Jose

Our guest house is located in downtown San Jose walking distance to Downtown San Jose, SJSU, Convention Center, Silicon Valley tech companies. It is behind the main house and has been fully renovated as has the entire property. Easy access to the private with everything you need to relax and vacation, or business travel. All around Public transportation like Light rail and Buses.

Guest favorite

A wooden deck is adorned with potted plants and a seating area. A light-colored cabana features an open serving space and is complemented by string lights overhead. The area is surrounded by greenery, offering a sense of privacy and tranquility.

Guesthouse in Atherton

4.88 out of 5 average rating, 125 reviews

Guesthouse near Stanford, Palo Alto, Menlo Park

You’ll love our place because of the ambiance, the privacy, the quiet, the outdoors space, the neighborhood, and the comfy beds. Our guesthouse is good for couples, solo adventurers, business travelers. We live in the primary house on the property. We are close to the CalTrain station (1 mile/10 minutes by bike). We carefully follow enhanced cleaning protocols.

Guest favorite

A modern kitchen features black cabinetry and stainless steel appliances, including a large refrigerator and a gas stove. A dining table is set for four, with white dishware arranged on gray placemats. Natural light enters through a nearby window, illuminating the space.

Guesthouse in Mountain View

4.98 out of 5 average rating, 168 reviews

1) 2BR/2BA Guest House near Downtown Mountain View

Simple, peaceful, and located close to freeways, restaurants, and shopping. You are booking the guest house labeled #A. This guest house has a detached primary unit that may be occupied. Please let us know if you have any issues with this arrangement. The only shared area's are the garage, driveway, and entrance to the property.